Most founders avoid this question until it's too late: Should you still be the CEO of your own company?
Mackie Swan was brought in by the three original founders of WOO More Play—a sexual wellness brand sold in Anthropologie, Nordstrom, and Revolve—to scale a business they realized they shouldn't be running day-to-day. Three years later, she's taken the business to profitability while navigating the complex world of "vice categories."
This isn't a conversation about sexual wellness products. It's about a decision many founders will eventually face: Am I the right person to be running the company I founded?
In this episode, we explore:
The "Capacity vs. Desire" framework: How to know if you've outgrown the CEO role
What the transition process actually looks like when bringing in an outside CEO
How to structure compensation and equity to align incentives
Why procrastination might be telling you you're in the wrong role
How to hire people who will actually tell you when you're wrong
What "vice categories" means and the hidden operational challenges (PayPal froze $50K+ of their funds overnight)
Why Mackie tracks EBITDA daily instead of typical vanity metrics
The difference between being a founder and being a CEO—and why they're not the same thing
Whether you're a founder questioning your role, considering bringing in outside leadership, or an operator thinking about joining an early-stage brand, this conversation offers rare insight into a transition most founders don't talk about until it's too late.
Guest Links:
WOO More Play: woomoreplay.com
Instagram: @woomoreplay
LinkedIn: Mackie Swan
I hope you enjoyed this episode!
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– Nate and the Profits on Purpose podcast team
Connect with Nathan Littlewood on LinkedIn: https://www.linkedin.com/in/nathanlittlewood/
Visit the Future Ready CFO website here: https://www.futurereadycfo.com/
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Welcome to the Profits on Purpose podcast, where we explore the journeys of purpose-led founders and the financial strategies that help them survive and thrive. Host Nate Littlewood sits down with eCommerce and CPG founders to unpack the real-life tension between a brand's mission and the practical realities of generating profit.